Hi @Jacob Tudor,I think I can help simplify this conundrum for you.You hired someone to do a job, and gave them the materials to do that job (your financial paperwork, etc, is the same as providing a painter with paint and paintbrushes).

Luckily my fiances step dad is a painter.

I learned this from my father who was a "building superintendent" (think janitor) for many, many years and even though the properties he managed had a plumber, electrician, painter, etc. on contract he was there to oversee any repairs on occupied rentals.   

At first I tapped drop cloths over the windows with finish nails complete with fancy little folds, but on my last house I used that white  painters' plastic and taped it to the exact shape of the glass.

They do enough volume that they have salaried electricians, plumbers, framers, painters on their team, so their costs are dramatically lower than what my wife and I can do.

Like when I mask the trim,I roll the painters tape all in one single piece leaving a portion of the adhesive side out and downward.

For the most part he has done that, but he also bought major tools to do the work such as a miter saw ($400) and a power painter ($320).

But painting is also considered a repair, and if you hire painters you can hit that price tag too.

If I have a painter do some patches, even if there are skilled, we will see a slight difference of color.Can I use the tenant deposit to repaint all the apartment?

Most painters I've met suck.